Crotonaldehyde → 5-(Propen-1-yl)-2-oxazoline-4-carboxylic acid ethyl ester
Reaction equation
[CH:1](=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH2:6]([O:8][C:9](=[O:13])[CH2:10][N+:11]#[C-:12])[CH3:7]>>[CH2:6]([O:8][C:9]([CH:10]1[CH:1]([CH:2]=[CH:3][CH3:4])[O:5][CH:12]=[N:11]1)=[O:13])[CH3:7]Participants
3
Procedure
The starting material is manufactured as follows: Reaction of crotonaldehyde with isocyanoacetic acid ethyl ester in a manner analogous to that described in Example 1 yields 5-(propen-1-yl)-2-oxazoline-4-carboxylic acid ethyl ester. By hydrolysis of the 5-(propen-1-yl)-2-oxazoline-4-carboxylic acid ethyl ester analogously to Example 1, 2-formylamino-3-hydroxy-4-hexenoic acid ethyl ester is obtained. Reaction of the 2-formylamino-3-hydroxy-4-hexenoic acid ethyl ester with thionyl bromide and subsequent treatment with triethyl phosphite in a manner analogous to that described in Example 1 (12 hours) yields E-2-formylamino-5-diethylphosphono-5-methyl-3-pentenoic acid ethyl ester.
Sources & evidence
- ORD record
- ord-bb2aa8c263a94987a6ba4a59539c1be9
- Source dataset
- uspto-grants-1992_12
- Patent number
- US05175344
Reaction notes
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